


2am

by supernatural_jackles



Category: Supernatural
Genre: F/M
Language: English
Status: Completed
Published: 2018-12-03
Updated: 2018-12-03
Packaged: 2019-09-06 14:37:26
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 10,790
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16834552
Author URL: https://archiveofourown.org/users/supernatural_jackles/pseuds/supernatural_jackles
Summary: Anon Request: Will you write a one shot where Dean and the reader are like each others weekly booty call with q lot of dirty talk?Anon Request: Can you do a rough Dean x reader? With a lot of dirty talk and kinky? Thanks!





	1. Chapter 1

**Author's Note:**

> Warnings: some feelsy stuff, dirty talk, temperature play, smut.

Dean Winchester.

The man was like no other man you had ever met. He was smart, handsome, loving, you could go on forever with all of the characteristics you loved about the man, but you’d be here for a lifetime.

You’ve know Dean for your entire life. You were his next door neighbor in Lawrence. His mom was best friends with your mom for years before you and Dean were even an idea. Dean was older than you by six months, and for a while, those six months were pretty significant. The difference between the big kid swing and the baby swing. He would smirk at you while his mom would push him on the swing while your dad pushed you in the little one. Dean would constantly bring up how he was older to you when the two of you were kids.

It stopped instantly when he lost his mom in the house fire. Dean’s dad was determined to find the thing that killed Mary, and your dad, who just happened to be John’s best friend, decided to set out with him. Your mom was going to go wherever your dad went. While the three of you stayed back in motels she would take care of you. Dean didn’t talk for awhile and even at that age, you could understand why. You would talk to him everyday, even if he wouldn’t say a word back. Sometimes he would smile softly at something you said, and that was enough to keep you going. After awhile, he came around, but most of all, he stuck to your side. He protected you.

Your mom was killed when you were eight, and Dean did the same for you. He was constantly next to you as you grieved. He hugged you a little longer before the three of you turned in for the night. You opted to sleep in his bed every night, feeling safe with his presence next to you.

When you both started high school, Dean walked with you to every class, and sat in the back with you. He was your best friend, the person you trusted the most in the world; he was your other half. It stayed the same, your father’s were hunting partners, which meant you went with them wherever they were heading to next. Dean was with you throughout everything.

Your father’s dropped you off at their friend Bobby’s house while they had a lead on the thing that killed Dean’s mom. Sam was happy to finally settle somewhere for a little more time, and focus on school. He told you and Dean that he wanted to go to college. You and Dean had no intentions of doing anything past high school. It was going to be you and Dean.

One night when Bobby was taking Sam to a movie, to reward him for getting an A+ on one of his tests, you and Dean stayed home. The two of you sat outside on one of the hoods of an old car in Bobby’s yard and watched the stars, something the two of you did often.

——————

_“Do you think our mom’s are watching over us?” he asked out of the blue. You turned your gaze to him, he was still focused on the sky._

_“Yeah, I hope so,” you said, “I think they’re together. They were best friends here, I think they would be up there together watching over the two of us.”_

_“I think you’re right,” he smiled, a comfortable silence returned between the two of you._

_“hey, umm, can I ask you something?” he rubbed the hair at the back of his neck._

_“You just did,” you smiled, “yeah, Dean. You can ask me anything.”_

_“Have you- uh- ever kissed anyone before?” he mumbled, you almost didn’t catch his question._

_“No, I- uh haven’t kissed anyone,” you answered. “Have you?”_

_“No, but I want to try it. I see people at school do it all the time,” he confessed._

_“I do too,” you whispered, hoping he wouldn’t quite catch it._

_“Would you- I mean we could- can I kiss you?” he stuttered, rushing through his words. You blushed at the thought of his lips on yours. You nodded your head._

_He turned to face you and you moved to make it easier. His hand came up to brush a stray piece of hair away from your face, and tucked it behind your ear. His thumb ran over your jaw as he leaned in, you could feel the heat of his breath blend with yours. Your heart was racing, you were nervous you were going to mess up. His lips touched yours faintly, sending a spark of electricity through your body. He pressed his lips fully onto yours as you kissed him back, your hand made its way to Dean’s waist. His hand cupped your cheek as you both melted into each other. It was perfect. He pulled away to watch your reaction, and all you could do was smile._

_“Wow,” you breathed out._

_“Wow, is right,” he smiled. “We were definitely missing out.”_

_“Yeah, we were.”_

_“I wouldn’t mind doing that again-with you,” he confessed, avoiding your gaze._

_“Yeah, only if it’s with you.”_

_——————–_

The two of you kissed often, whether it was before the two of you entered your class, or before the two of you headed to bed for the night. Not to mention lunch times you spent together, exchanging kisses while the two of you ate, or when Bobby went out to get some groceries, Dean would come into your room and kiss you until Bobby got home. It wasn’t long after that when Dean asked you to go out on a date with him, and of course you said yes.

The two of you were inseparable after that. You held hands in the hallways at school, and he wrote you cute little notes during class. It didn’t feel any different to when you two were friends, the only difference was that you could kiss him whenever you wanted and you went on dates every Friday night. For awhile, you forgot about the hunting life outside of your relationship with Dean, and it felt normal; it felt good.

Of course your dad’s came back and you had to move to the next motel, and you weren’t completely unhappy about it. It just meant that you and Dean could share a bed again. The first night, he was a little unsure of how you would react to him wanting to hold you through the night, so he waited for you to make the first move, and you did. You fell asleep on his chest while he had his arm wrapped around your shoulder. He said the next morning he hadn’t slept that good in such a long time.

The both of you had lost your virginities to one another. You opted out on going to prom, both of you said it wasn’t your thing and decided to stay in, save money and spend that time together. You ordered in chinese food, and he picked out an old western to watch. When all was said and done, you lay in bed together, kisses became more passionate, the simplest touches had you aching for more. He carefully removed all of your clothes as you did him, it was the first time you had seen each other naked as well, all of it was so intimate and you hadn’t even started. He took his time getting to know every inch of your body, kissing and touch every inch before you could do the same. He took things very slow, and soon you realized why they called it _making love_. You realized that you were completely in love with him. He made sure that you were comfortable the entire time, never pushing you to do something you weren’t okay with. When the two of you finished, he kissed you for what seemed to be hours.

You were together for years after that. He was there for you when you lost your dad to the yellow eyed demon, who was known as the one who killed Mary and your mom. You were there when he took John away from Dean and when Sam was killed. You cried with him when he told you he made a deal with a demon to bring Sam back. You were furious with him for a week, and he understood, but he promised he’d find his way back to you.

Sam picked up the pieces when Dean died. He stuck with you for a few weeks before deciding to go with Ruby to find Lilith. You on the other hand, went to Bobby’s.’=

————–

_“Kid, you’re going to catch a cold sitting out in the rain like this,” Bobby said as he walked over to you. You were sitting on the car that you and Dean watched the stars on. Dean had only been gone for two weeks._

_“I don’t care, Bobby,” you said coldly. “He was my other half, for my entire life.”_

_“I know you’re hurting, that won’t just go away. But you can’t spend the rest of your life stuck here,” he told you._

_“This is where Dean kissed me for the first time,” you voiced calmly, “you went out with Sam. Dean and I liked watching the stars. Then he asked me if I had ever kissed someone. Of course I was only fifteen at the time, and Dean was the only boy I had ever wanted to kiss. I told him no and he asked me if he could kiss me and he did. Bobby I would do anything to feel that again. To feel him close to me, to feel his skin brush against mine. I wake up every morning in hopes that this is some kind of nightmare. Then I turn to see the other side of the bed empty and it barely even smells like him anymore. I just want him back so bad.”_

_——————–_

When Dean came to Bobby’s door, you didn’t even have to test him to know it was him. You saw the pain in his eyes, there was no way a demon could even fake that. You instantly jumped into his arms and burst into tears, holding him tightly to you, afraid he would disappear if you let go. You saw the tears in his eyes when you pulled back before you kissed him hard.

You stuck together through everything. He was very stressed out and worried about Sam with Ruby, and he was thankful to have you to talk to about it. When Sam brought the apocalypse on, you help him fight off the urge to say yes to Michael, which was difficult to do. The worst was when Sam said yes to Lucifer and jumped into the cage. It was really hard on him then. You spent months trying to help him cope with the loss of his brother, and when he was finally back on his feet, he thanked you for it. For that year, the two of you quit hunting, settled down in california near the beach and spent a lot of time in the sun. That is, until Sam came back without a soul.

Everything was good until Dean ganked Dick Roman, and sent him god knows where. You spent half of the year looking for him on your own since Sam had given up. You came up with nothing. You settled in an old cabin of Bobby’s, taking hunts whenever you could. Which brought you here, sitting next to Dean in an old bar.

The two of you were together for what seemed to be seventeen years. Now the two of you were friends, friends that slept together. You just learned a few month ago that he went to Purgatory and got back a year and a half ago, and didn’t tell you. You were hurt, but Dean had spent so much time with you, that maybe being apart wasn’t such a bad idea. Maybe he was tired of being with the same girl his whole life.

“Well, here’s to a successful hunt,” Dean smiled as he held up his bottle of beer. You and Sam held yours up to his before you took a long swing. It didn’t hurt to be around him as much anymore, you had healed for the most part. And having him as your friend was better than not having him at all.

“Hi there, handsome,” the busty blonde bartender said as she walked up to Dean. You turned to avoid the whole conversation. It happened a lot when Dean went to bars. He often left with them too, but that wasn’t your business anymore. It only concerned you when Dean called you every other week to come sleep with him. And when he didn’t call, you’d call him to come over. The silent agreement.

Dean talked with her most of the night, while you had a few guys come up and talk to you, you weren’t interested. You didn’t want to have sex with some stranger. You nursed your beer and talked to Sam about weird cases throughout the years before getting into stuff he learned in college when he went.

“Can I get the tab please,” Dean’s voice broke your conversation.

“Heading out with the bartender?” Sam asked.

“Nah, she’s definitely not the one I want to take home tonight,” he started, his eyes locked to yours, “she talks way too much, plus, she’s not my type.”

Sam drove the impala home while Dean sat shotgun and you in the back. You arrived back in your room just before 2am. Your jacket shed from your body and threw it onto the chair. You quickly changed out of your clothes, and turned the shower on. You were covered in sweat from today’s hunt and the smell of cigarettes mixed with cheap alcohol was etched into your skin.

You quickly dried off and threw your pajamas on; a pair of shorts and one of Dean’s shirts he let you have. You heard a faint knock on your door just as you were about climb into bed. You opened it to find Dean standing at your door in a white-fitted tee and his plaid pajama pants. His hair was wet from his shower.

“Dean, come in,” you smiled softly. He walked in and you closed the door, locking it behind you.

His lips were on yours in an instant, his arms snaked around your back, pulling you flush against his muscular body. He picked you up with ease and pressed you against the wall, his fingers pressed hard into your waist, enough that you are likely to find bruises in the morning. His hips were pressed to yours, and you could feel his growing member pressed against your center. You kissed him hard as you trailed your fingers down his torso, lifting the hem of his shirt up, breaking the kiss momentarily to discard his shirt from his body. You could never grow tired of seeing how perfect his body was. He practically ripped the shirt over your head, revealing your bare chest to him. He groaned in approval before capturing your lips in his.

You ground your hips over his flannel clad erection, moaning into the kiss. The friction your bodies created was phenomenal, every inch of your body was craving Dean’s touch. He quickly made his way to the bed, throwing you on top of it. His fingers made their way to the waistband of your pajama short and before you knew it, they were being torn from your body, your panties along with them.

He kissed along the sensitive skin of your thighs, the stubble on his face only teasing you, making you squirm under his touch.

“Dean,” you moaned.

“Patience, sweetheart,” he smirked. His fingers brushed over your folds, you bucked your hips, wanting him to touch you more. “You’re so wet, Y/N. All for me?” you nodded.

“All for you Dean. I want you. I need you,” you practically begged.

“I’ll give you anything you want,” he grinned.

One of his fingers entered your center while he pressed his lips to your bundle of nerves before his tongue swiftly ran over the bud, sending pleasure throughout your body. Your hand made it’s way to his hair, holding it tightly as he licked at your folds. If there was one thing Dean Winchester was good at, this was it. His finger entered you once more and began to brush over your sweetspot. You were growing closer and closer. He added another digit, it wasn’t even fifteen seconds before he had you a shaking mess in front of him, calling out his name.

“I love it when you come around my fingers,” he whispers into your ear, “and I love licking you clean as you do.” His voice was at a low growl, his words causing heat to pool in your stomach once more.

“Dean, I need you,” you cried as your hands made contact with his skin.

“What do you want, Y/N? Tell me what you want me to do,” he groaned.

“I want your cock, Dean.”

“It’s yours,” he smiled as he sat down next to you on the bed.

You got off the bed and walked to the motel fridge, which just happened to have a freezer. You took an ice cube out of the tray and placed it in your mouth, sucking on it for a few seconds before making your way over to Dean. You straddled his hips, leaning down to his chest area before placing your lips to his tattoo. You removed the ice from your mouth and placed it on his chest, causing him to tense up momentarily. You dragged the piece of ice with your lips over his pecs, leaving it in the center before running your cold tongue over one of his nipples. His hands were immediately on you, his breathing picked up, you could tell he was enjoying your sudden boost in confidence.

You took the melting piece of ice between your lips and continued to trail it down his body, stopping near his belly button. Your mouth still felt cold, which meant it was the perfect time to tease him the way he teased you.

Your fingers curled in the waistband of his pajama pants and boxers, making quick work at removing them from his body. His erection sprang free, the tip leaking pre-cum. It took all you had not to run your tongue over the top, but you wanted to tease him. You took him in your hand, gently stroking his hard length.

“Y/N, please,” he growled.

“Did I make you this hard, Dean?”

“All you. It’s all for you, Y/N.”

You ran your cold tongue on the underside of his cock, his breath hitched, his body shuddering at the cold contact and pleasure. You decided not to tease, you wanted him. You licked over the tip of his cock, tasting the pre-cum on you tongue. You wrapped your lips around the tip, sucking gently as his hands made their way into your hair. You could feel the heat of his cock on your cold tongue as you careful took more of him into your mouth. Your hand made work of what you couldn’t fit into your mouth. You continued to bob your head, feeling him hit the back of your throat. His breathing became erratic, a clear sign that he was close.

“Y/N, please stop, I’ll come if you don’t,” he warned. You released him with a pop and climbed up on the bed and lay next to him. He got up of the bed and grabbed a piece of ice from the freezer and a condom from your bag before heading back to the bed. He placed the piece of ice between your breasts, then his lips were attached to your neck, the coldness of his tongue caused you to shiver, goosebumps covered your body. You could tell your nerves were on edge.

He trailed the melting ice cube over each of your breasts. His fingers played with the hard bud, while his frosty tongue ran over the other one, sending a wave of pleasure that you had never experienced before. His hands touched every part of your skin before he threw away what was left of the ice.

He rolled the condom over himself, then moved over top of you, his cock lined up with your entrance. He leaned down to kiss you quickly before pushing into you quickly, filling you up completely.

“You okay, Y/N?”

“I’m good, you can move, Dean.”

He pulled out almost completely before slamming back into you. The pace was fast, his entire body weight was pressed against yours. His hands held you tightly, his fingers digging into your skin as he pounded into you.

“You’re still so tight, god I love it. You feel so good,” he breathed out between thrusts.

“I love the feel of you inside me, Dean. So big, so good.”

The sound of skin slapping filling the room, along with the sounds coming from the two of you. You wrapped your legs around Dean’s waist, giving him a new angle. His cock was hitting your sweet spot with every hard thrust.

“You like that ba- Y/N? You like it when I dig my fingers into your skin while I fuck you?”

“I love it, faster Dean. I want to feel it in the morning,” you begged. “I’m so close, make me cum Dean. I want to come around you.”

Your bodies moved together, the sweat making your skin slide against his. He hit your sweet spot hard, your nails digging into his back and you threw your head back in pleasure, crying out his name as he continued to slam into, feeling your walls clench down around him. He was panting, releasing small moans each time he breathed out. It only added to the pleasure. His hand made it’s way to your clit, white hot ecstasy ran through your veins.

Dean buried his head in your neck, his fingers grasping onto your sweaty skin as he spilled himself into the condom, he moaned out your name into your ear as he thrusted inconsistently into you.

He lifted his weight off of you, quickly discard the condom into the trashcan beside the bed before climbing back over to you. You didn’t know why you did this to yourself. You were still completely and utterly in love with the man, and the two of you weren’t together anymore. This was just sex, but each time it felt like it was something more. You loved sex with Dean, and this was as close as you were going to get to him, and that was when he wasn’t with someone else. All you’ve ever had was Dean, and he was all you ever wanted.

You turned to face away from him, you felt the tears pool in your eyes, and the last thing you wanted was him to see you cry. You felt a strong arm wrap around your waist, pulling you closer to a warm chest that was now pressed against your back. He began to kiss at your neck, something he usually didn’t do when the two of you hooked up. His lips traced up to your jaw, his fingers brushed the hair away from your face before he placed a kiss to your cheek.

His hold on your waist turned you to face him in the dark. His lips pressed gently to yours, identically to the first time he kissed you all those years ago. Your lips moved lazily together, his hand coming up to hold yours. It felt like the two of you were kissing for hours, just like you did the night you first had sex. The memories came flooding back to you and you pulled away and lay in silence.

“I want you to know, I-uh, haven’t been with anyone other than you, Y/N,” he murmured as he gingerly brushed the hair away from your face.

“But I thought-”

“No, I can’t. It’s only ever been you,” he told you.

“Why?” you inquired.

“Because they’re not you. No one compares to you, not even close,” he states before placing a kiss to your forehead. “Get some sleep, we can talk in the morning. I promise I’ll still be here.”

“Okay,” you frowned. “Good night, Dean.”

“Good night, Y/N.”

He lay on his back, wrapping his arm around you, pulling you to his chest. You rested your head on his chest. You were slowly being consumed by sleep when you heard those muffled three words for the first time in twenty years. 


	2. 10am

**Notes for the Chapter:**

> Warnings: angst

Dean Winchester. **  
**

The first thought that comes to your mind every morning when you wake up, and the last thought that crosses your mind before you fall asleep. The only person that could make you question everything in an instant, the only person who could make your heart race a mile a minute. The only person you wanted… but couldn’t have, not fully anyways.

You opened your eyes, the sunlight shining through the motel room curtains, projecting light onto the wall above your bed. You head lay on Dean’s bare chest, his heartbeat beneath you, calming you to a whole new level. His arm was securely wrapped around you, it was like nothing had changed between the two of you. If only.

You lay there, content with your surroundings. Dean began to rub small circles on your arm, sending shivers down your spine. You nuzzled into his chest, feeling the warmth of his body press against yours.

“Good morning,” he said, his voice still raspy from the previous night’s sleep.

“Morning,” you smiled. Then you remembered last night’s events. Your body was a little sore, god knows how many bruises he left on your body. But most of all, he promised he’d be here in the morning, to talk. “I’m going to go take a shower.”

You arose from the bed, Dean’s touch lingering on your skin, even after he let go of your body. This was going to be a hard day, you could just feel it.

You stripped from your clothes and got in the hot shower, hoping to feel the slightest bit better. You eyes felt heavy, you heart heavier.

“ _Dean, what are you doing in here?” you asked, excitement filled your voice. Dean’s hands were on your hips the second you turned to face him._

_“What? Can’t a guy shower with his beautiful girlfriend?” he smiled before pressing his lips to yours. “Besides, you shower in hot water and by the time I get in, it’s freezing.”_

_“What if our dads come home, Dean? What if Sam walks in on this? He’ll be home from his friends house any minute,” you protested._

_“Then I guess we’ll have to clean ourselves quickly,” he winked, “Damn I could get used to looking at you naked.”_

_“Oh really?” you raised your eyebrow. “I must say the same for you, Winchester.”_

All your thoughts went to that morning; the morning after you and Dean had sex for the first time. The way he held you so tightly to him when you shared the shower together. His hands wandering over your body while he washed your body, so delicately and precise. His eyes were locked on you as you washed over his body. The two of you giggled as you covered each other in bubbles. A tear slipped down your cheek, oh how you wished you could go back.

You got out of the shower, taking your time to dry off and put your clothes on, hoping to prepare yourself to say goodbye to Dean for a little while. He’d come around in a little while, stay for a bit and walk away again.

You opened the door to find an empty motel room, no sign whatsoever of Dean. You grabbed your duffle bag from the couch and began to shove your stuff into it. You tried everything to keep your mind off of him, but that was the hardest thing to do.

“Hey, you’re out of the shower. You usually take longer than that,” he said as he walked in the door of the motel, a paper bag in one hand, a tray with two coffees in the other, using his foot to close the door. “What? Did you think I would leave without talking to you before I left?”

“Kind of. It seemed that way,” you told as you continued to pack your bag.

“I wouldn’t do that to you. Ever,” he stated. “I got you your favourite, and a coffee with milk, just the way you like it.”

“Thanks, Dean,” you smiled. “So do you want to talk now?

“Yeah.”

—————-

_“Y/N, what’s wrong?” he asked you, worry took over his body._

_“I have to tell you something, and I don’t want you to freak out,” you began, tears filled your eyes._

_“You can tell me anything, Y/N. You know that,” he assured you, he took your face in his hands and kissed you quickly. “Talk to me.”_

_“I’m late, Dean.”_

_“Late as in late?” he asked._

_“Yeah, two weeks,” you sniffled, “I’m really scared, Dean.”_

_“Shh, I know. It’s going to be okay. I’ve got you,” he said as he pulled you in for a tight hug. He held you as you cried into his neck, never loosening his grip. “We’ll figure this out, Y/N. We’ll do this together. We’ll go out and buy like ten pregnancy tests and take them all. I’ll even take you to the doctors to be sure. “_

_“How are you so calm right now,” you chuckled as you wiped your nose with your sleeve._

_“I’m terrified as hell right now. But it won’t help you at all if I freak out now will it?” he chuckled. “We may only be eighteen, and our dad’s are definitely going to kill us if you are. But we’re going to do this together. I am by your side through this whole thing. I will always be by your side.”_

_“Promise?”_

_“I promise.”_

_——————-_

“Where are you headed to next?” you asked.

“Not sure yet. There aren’t any cases we’ve caught wind of yet. What about you?” he inquired as he took a sip of his coffee.

“I don’t know, maybe out west. I just kind of drift around,” you told him.

“You know, I don’t think I ever apologized to you for not coming to find you as soon as I got out of Purgatory,” he began, his eyes locked to yours.

“You did, Dean. It’s okay.”

“No, it really isn’t. You ar-were my girlfriend, Y/N. You were my girlfriend for seventeen years, you’ve been my best friend forever, literally, and I should have come to find you as soon as I got out,” he stammered on, his hand running over his face.

“Then why didn’t you?” you questioned, tears welling up in your eyes.

“I thought you got out of the life, Y/N. I found Sam, and he said he had no idea where you were. I knew he didn’t look for me, and he said that he hadn’t heard from you since the day I went missing. I figured you looked and gave up. No one had heard anything from you in months so I figured you got out. I wasn’t about to come and take that away from you, not yet anyways. I was going to wait until I got out until I would come and find you,” he paused, “Then I heard that you just took out a vamps nest up in Illinois and I hauled my ass up there to find you.”

“But I didn’t see you until we met in Sioux Falls two weeks later,” you mentioned.

“I know. I followed you around for two weeks just to see if you had someone new in your life. I wasn’t about to ruin that for you by showing up if did. When I found out you didn’t I walked right up to you.”

“I never moved on, Dean. I’ve spent my entire life with you. You were my boyfriend for seventeen years. You were my first everything Dean. Do you really think that I could just move on from that?”

“No, in all honesty, I didn’t think you would. You’re not that kind of person, and I know you don’t give up that easily,” he smiled.

“So what about you then. Sam seems to think that you’ve moved on, quite a bit by the sounds of it,” you brought up.

“I told you last night, you’re still the only one I’ve been with. Sure Sam has seen girls flirt with me, just like the one at the bar last night. I’ve left with them yes, but never brought them back to my place. I got in the car and drove to their place, and I just didn’t want to, I couldn’t. They weren’t you, not even close. And the only person that I ever want to be intimate with, is you. It’s always been you Y/N.” he described. “And I know for a fact that I’m the only one you’ve ever been with. You’ve always been a one kind of guy, girl.” A tear slipped down your cheek.

“You’re right. It only has been you,” you confirmed.

“I can’t just sleep with you and walk away anymore, Y/N. These weekly calls between us, wanting one another to come and meet. The rough sex in the backseat of the impala, or in the bathroom stall in run down bar, the sketchy motel room beds. I can’t keep doing this. I can’t keep hurting you like I know I’m doing,” he paused. “I can see it in your eyes each time, and last night I saw tears. I made myself and your dad a promise that I would never be the reason you’re crying, that I would never be the person to hurt you, and I’ve broke that. I can’t keep doing it to you, it’s not fair.” You nodded your head, wiping away the tears that escaped.

“So this is it, then?” you said sadly, “this is goodbye?”

“No, not if you don’t want it to be,” he voiced quietly. You could see the tears fill his eyes. “I’ve hurt you so much, especially in the past few years. But all I know is that I can’t live without you. I don’t want to live without you. You’re my best friend; my other half and have been for as long as, well you have lived, since I’m older. You’re all I know, and I’m lost without you. You and I both know that this is not just some hook up. You have my heart, Y/N.” he said, his voice fading to a whisper as he grew closer to the end. “We’re heading out today at 2, there is definitely a spot for you next to me, and there’s a room with your name on it in the bunker. I’ll give you a couple of hours to think about it. If you can forgive me, I promise I will spend the rest of our lives trying to make it up to you.”

“Okay, I’ll think about it,” you smiled softly at him.

“That’s all I ask,” he smiled weakly. “If you decide not to, I completely understand. Just know that I’m going to miss you, everyday. And I really am sorry. Take care of yourself, gorgeous.”

He brushed the hair away from your face, tucking it behind your ear. His hand came up to your cheek, his thumb brushing over your jaw, just like he did the first time he kissed you all those years ago. He carefully pressed his lips to yours. Your hand made its way to his waist. He pulled away and pulled you in for a tight hug. He pressed his lips to your forehead before pulling away completely. He took your hand, placing something in it, then he walked to the door. He smiled softly, his cheeks stained with tears as he opened the door and left the room.

You opened the small piece of paper he put in your hand, your heart stopping momentarily as you read the words on the ripped sheet.

_**I love you, Y/N. Always have, Always will. -Dean**_


	3. 2pm

**Notes for the Chapter:**

> Warnings: Slight Angst, Fluff, Smut

Dean Winchester.

The man could have you in a pool of your own emotions almost instantly. He was constantly surprising you, just when you thought things couldn’t get any better, he’d do something to make you wonder what else he was capable of. He loved with his entire heart, you could see it in the way he was with Sam, and sometimes in the way he was with you. His heart was so big, and he spent all of his time making sure that you and Sam were happy, leaving no time to make sure he was.

Even after all this time, Dean was still capable of taking your breath away and making your heart race a mile a minute. His bright smile still melted your heart, you still felt safe in his arms. The smell of whiskey and gunpowder would instantly calm you down. You’d think it would have gone away, especially with knowing Dean for all thirty-two years of your life, and you dated him for seventeen of them; that’s more than half of your life.

He wasn’t wrong in saying that he had hurt you, especially over the past year and a half, though you did feel a little better knowing that you were still the only one that he was intimate with, but it still hurt to know that he didn’t look for you. You spent your entire life with him, the least he could have done was called to tell you. You would have come running to him.

Maybe that’s why he didn’t. He didn’t tell you because he didn’t want you to know. Yes he wanted you out of the life, but you wanted to get out with him, and there was no way you would get out without him. What if it was his way of letting you down easy? What if he just didn’t want to be with you anymore?

You stared at the small piece of paper in your hands. Those words you’ve been waiting to tell him since you were seventeen. Those words that he’d never expressed to you. They were written so simply, as if they had been written a million times before, only they hadn’t; not once. Your heart fluttered at the thought of it, the butterflies were soaring in your stomach, it almost hurt.

———————

_“Come on, Dean. Talk to me. What’s going on in that gorgeous head of yours?” you asked as you kneeled between his legs. He buried his face in his hands before looking at you._

_“What is there to talk about?” he brushed you off._

_“What you’re thinking about? The hunt maybe? I know how personally you take things like this. Let me in, let me help you,” you said as you drew small circles on his forearm with your thumb._

_“Like anything you could say would help, Y/N. Just do us both a favour and stop trying!” he yelled as he got up and made his way across the room._

_“Dean, I thought we were in this together. I was just-”_

_“Yeah, well I’m was getting sick of this whole together thing anyways,” he confessed as he grabbed his jacket and made his way out the door, slamming it behind him. A tear slipped down your cheek._

————————–

You and Dean had your fair share of fights, some were stupid little ones that you both soon realized weren’t worth wasting your breath over, but some were so bad that you didn’t think that the two of you would ever recover. The two of you would go at it until you were blue in the face. You’d walk away and let yourself cooldown. You wouldn’t face him again until you were in a better mindset. You hated fighting with him, it was one of the worst things and knowing he was mad at you, definitely not a good feeling. When you had enough time to settle down, you would go back and see if you could work things out with him. Sometimes you would be able to apologize and all would be okay, and other you would just end up fighting again. Those were the worst.

—————————

_“Dean, how the hell could you not tell that bartender was flirting with you?” you said loudly, trying to keep calm._

_“She was not! I don’t see what the big deal is. We were talking Y/N, nothing more. God what is going on with you?” he replied._

_“Are you happy in this relationship, Dean?” you asked._

_“Of course, Y/N! Why wouldn’t I be?” he said defensively._

_“I just feel like every time we go out, you always talk with some attractive, skinny and beyond perfect girl to talk to. I feel like this isn’t enough for you anymore, like I’m not enough for you anymore,” you explained. “I get it though. I mean we’ve been together for six years, I’m all you’ve ever experienced and I get that you would want something different.”_

_“Y/N, this is crazy!”_

_“It’s not crazy, Dean. I’m just sorry I’ve been holding you back,” you voiced quietly._

_“Y/N!” he yelled as you made your way out of the motel room with tears in your eyes._

_You walked down the road from the motel, trying to clear your head from the heated words exchanged not so long ago. You knew it was only a matter of time before he realized that you were only holding him back. His eyes were already starting to wonder, you just hoped that he would soon realize and not trail you along._

—————————-

The only thing that you enjoyed about fighting with him was the making up part. Sometimes it took a little longer than others, but it was still the best part. The tension had dissipated, any anger that was held had now vanished. The two of you sat down and talked to each other, or sometimes you saved the talking until after. He would hold you to him, kiss you sweetly and tell you that he was sorry. The two of you would kiss for the rest of the night, your bodies entangled in one anothers. He would make love to you as if it was the last time he ever would. His hands would travel over each spot before he attached his lips to your sensitive skin. Your breaths mingled with one another as you moved together. When you both had calmed down, he’d press his lips to your forehead before he’d talk to you.

————————

_“Dean?” you said quietly. He looked up from his computer at you, you could tell he was still upset with you._

_“Yeah?” he said coldly._

_“I’m sorry. I shouldn’t have pushed you to talk to me, hell I shouldn’t push you to talk to me when I know you don’t want to. I was just trying to help, but I know I was only making things worse. I just thought I should tell you that. You can go back to what you’re doing now. Good night, Dean,” you spoke softly, tears threatening to spill over your cheeks. You climbed into your bed facing away from Dean and towards the wall._

_You weren’t expecting Dean to apologize. He shouldn’t have to for the way he was feeling. He told you he was tired of you trying to help him when all you did was make things worse. He didn’t to be in this relationship anymore. There was nothing you could say or do to fix that. There were no apologies needed for that._

_You felt a dip in the bed as someone else’s weight was added. It took all of your strength not to turn to look at the face behind you. You knew it was Dean. Sam never overstepped his boundaries. He knew you well and knew that you just wanted to be left alone, not to mention he wouldn’t do that with Dean in the room._

_You felt a strong arm wrap around your waist as a tear made its way down the side of your face. He leaned over and pressed a kiss to your cheek before squeezing you tightly._

_“I’m so sorry, baby. You didn’t need to apologize to me. I get that you were just trying to help me, and I shouldn’t have been a dick and pushed you away. You don’t make things worse, you make things better, you always have,” he whispered, “and I’m not sick of this whole together thing. I never could be. You’re the best girlfriend in the entire world and I don’t deserve someone as good as you. I’m sorry for ever making you feel like you were anything less than the best person I know. Good night, sweetheart. I hope you can forgive me.”_

_You shifted to face him and buried your head in his chest. No words were exchanged, you just held onto each other as the world faded away._

————————-

There was one particularly bad fight the two of you had that you had never quite been able to get over. It was more of a fight with yourself than it was between the two of you, but he was involved none the less. It always came down to you feeling insecure about yourself. Dean would be surrounded with beautiful women that are literally throwing themselves at him while you on the other hand were invisible. You never stood out to anyone except for creeps. You knew that if you hadn’t grown up with Dean, you would have had no chance in hell with him. Most days you still wonder why he was with a girl like you when he could have anyone he wanted.

That’s when you decided. You weren’t going to go back with him. Dean deserved so much better. There were things you couldn’t give him. There was no way you were ever going to get over your insecurities, and that would sink your relationship down even further. Dean didn’t need to reassure you every time that you were beautiful, and perfect and everything he ever wanted in his eyes. He was going to get tired of doing that just like he did before. It was probably one of the reasons he didn’t come find you right away in the first place.

It hurt, it definitely did. He was all you ever wanted, but it would be extremely selfish to drag him down with you, again.

—————————-

_It had been hours since you last spoke to Dean. Hours since that fight between the two of you and harsh words were spoken. You knew you had to go back, Sam and Dean were probably worried sick about you. You had finally calmed down, now it was time to head back._

_You opened the door to the motel room, it dimly lightened, as you looked around you saw candles surrounding the room. Neither of them were to be seen. You shed your wet coat and placed it on the chair as Dean came out from the bathroom. His hair was wet from his shower, a towel hung low on his waist._

_“Thank god,” he said quietly before making his way over to you. His lips met your instantly as he held your body close to him. “I was so worried about you.”_

_“I’m fine, Dean,” you assured him._

_“I’m glad. I’m so sorry Y/N. This is all my fault,” he started. You shook your head._

_“Dean-”_

_“No. I need to get this out okay. You are not holding me back! Not even close okay? I don’t want you to think that. I also don’t want you to think that you’re not good enough for me, because you are; you’re too good for me in fact. Y/N, yes we’ve been together for six years but you have to know that I wouldn’t trade them for anything. You are everything that I have ever wanted. You’re beautiful and smart and caring. You put up with all of my crap, and you don’t look at me like I’m some sort of idiot. Those skanks at the bar have nothing on you. You’re all I want,” he explained._

—————————-

You looked down at your phone, the time read 1:56. You knew they would be leaving in a few minutes and you couldn’t help but think if you were making the right decision.

Your phone went off, looking down to see Sam’s face pop up on your screen. Why on earth would Sam be calling you? You pressed the little green button and held the phone to your ear.

“Sam?” you asked.

“Dean, come on. You are miserable without her and you are just willing to walk away from it?” Sam shouted. Did Sam pocket dial you?

“You don’t get it Sam,” Dean said.

“What don’t I get Dean? I see the way you are with her Dean. The way you still look at her after being with her for seventeen years. I know damn well that you didn’t sleep with any of those girls because they aren’t Y/N. Lets face it Dean, she’s all you’ve ever known and you can’t forget that. You don’t want to.”

“You don’t think I know that Sam? But I don’t want to force her to be with me. I want her to be with me because she wants to, because she loves me. Not because I want to be with her,” he told.

“You love her, Dean. I can see that you do, and you have for awhile. I don’t see why you never told her,” Sam mentioned. “I don’t see why neither of you said it.”

“Yes I do love her, but that’s not enough. I gave her a piece of paper saying that I loved her before I walked out of the room,” Dean told him.

“You didn’t say it to her?”

“No, but if she chooses to come with us. I’ll be damn sure to tell her every god damn day until I die,” he said softly. “I just want to be with her. It’s always been her, Sam. I’m lost without her and it’s going to hurt like hell if she chooses not to come with us.”

“Just go to her room, Dean. Go tell her everything.”

“I can’t. She needs to do it on her own. I’m going to the car, pack up and meet me out there.”

You hung up the phone and threw it on your bed and began to throw your things into your duffel bag, not caring that they weren’t folded. All you knew was that you wanted Dean, and that you loved him. Nothing else mattered.

You did a once over around the room, checking that you got all of your stuff. You checked the time, and realized that it was 2:07. Surely he would have waited a few extra minutes. You quickly grabbed your bags and headed out the door. That’s when you noticed the impala was gone.

You hoped to god that one of the boys had the GPS on so that you could track their phone back to the bunker. You threw your bags in the back of your old mustang while your phone searched for their whereabouts. Thank god you were able to track them.

You were on the road within minutes. You wanted to get to them as soon as possible, get to Dean as soon as possible. He was probably thinking that you didn’t want to be with him, that you didn’t love him back. You just wanted to be able to hold him and kiss him like you used to be able to do. He was probably heartbroken at the moment.

You followed them six hours to Lebanon, which is where they stopped. You figured they had to live somewhere around here. You trailed the bumpy road to an old building, most of it looked to be underground. Then you saw the impala, relief washed over your body. You were finally here and minutes away from seeing the love of your life.

You climbed out of your car, leaving your bags in the trunk. They weren’t your top priority. The rain came pouring down as you ran to what seemed to be the front door. You hit it hard, hoping that someone would hear you. The door opened, revealing Sam.

“Y/N,” he smiled, “I’m so glad to see you.” He pulled you in for a tight hug before closing the door behind you.

“I’m sorry I took so long. I was planning on joining you guys but I took a little too long to pack and by the time I was done, you guys already left,” you told him. “Where is he?”

“He’s in his room. He’s not doing so good. He didn’t speak a word to me the whole ride back,” Sam told you. “I’m hoping you heard the phone call.”

“I was meant to hear that?”

“Yeah. I called you on purpose. You needed to know that he really does love you. I know you, and you definitely overthought everything. You both are meant to be, now go be with him. Better yet, go tell him you love him,” he said.

“I will. Umm where is his room?” you asked.

“Just keep following the halls, his room is number 11. I’ll be going out for a few hours.”

You nodded your head and headed down the hall, following the numbers. There were so many rooms in the bunker, so many things that you couldn’t wait to explore. You finally arrived at door number 11. You stopped dead at the door, taking a deep breath, trying to compose yourself before knocking on his door.

“Go away, Sam. I don’t want to talk,” his muffled voice said. It was quiet, you could barely hear him, but from what you could make out, he was really hurt.

You carefully opened his door, quietly making your way into his dark room. You eyes wondered around the room. A light dimly brightening the room. He had guns hanging on the wall, a few books open on the desk and beside his bed were pictures of his family, and one of the two of you together. He lay on the bed, facing away from you.

You climbed onto the bed, he made no movements to look at you. You then wrapped your arm around his waist, and pressed a kiss to his cheek, then his temple.

“I love you, Dean. Always have, always will,” you whispered into his ear. “So you are stuck with me, forever.”

He rolled over to face you, his eyes were red and puffy. You swore your heart broke right then. You leaned in and press your lips to his, he responded immediately. You pulled him in close to you. His hand made its way to your face, cupping your cheek as his lips worked in sync with yours. He pulled away and pressed his forehead to yours.

“I love you so much, Y/N, and I should have told you seventeen years ago,” he muttered.

“Even though you never said it, I knew you did.”

“Good. Thank you for coming back to me, I thought you wouldn’t for a while there,” he said sadly.

“I almost didn’t, I began to let my thoughts get the better of me, but seeing you like this, I’m so glad I didn’t let them. I’m so sorry for hurting you like this, Dean. I spent forever packing all of my stuff and by the time I got out, you had already left. Thank god Sam had the GPS on, or else I wouldn’t have been able to find you.”

“I’m never letting you go. You’re mine forever,” he smiled.

“Kiss me, Winchester,” you asked him, “we have a lot of time to make up for.”

“Yes, ma’am.”

He leans in, his lips connect to your softly. His grip on you tightens, afraid that if he lets go of you, this would all be a dream. He takes his time, making sure you were comfortable enough, making sure you felt every emotion he poured into his kiss, and you did. You could only hope that he was feeling the same way.

He pulled away, and began to help you out of your semi-damp clothing. He took his time, his fingers dragging over every inch of your skin as the material was removed from your body and added to the floor. You trailed your hands beneath his shirt, feeling the heat radiating off of his body. You were left in your bra and panties, his eyes roaming over your body, stopping at the dark marks left on your body from earlier on.

“I’m so sorry I was so rough with you. Does it hurt?” he asked, concern filling his eyes.

“I’m okay, I didn’t mind it, though maybe not tonight. They are still a little sore,” you told him.

“Okay. I wasn’t planning on being rough with you. If anything, I was hoping we could take this as slow as possible. I want to make love to you,” he confessed.

“I’m okay with that. I just want to be with you Dean,” you smiled.

He hovered over you, pressing his lips gently to yours, his hips pushed into yours and you could feel his growing erection in his pajama pants against your center. His fingers trailed lightly over your body, sending chills down your spine. You helped him out of his shirt, throwing it to the floor before pulling him against you. His full weight was resting on top of you and you loved it. You felt so safe, and warm. He was alway careful when he did, making sure you were comfortable since he weighed more than you.

“I love you,” you whispered.

“I love you, too,” he smiled as he kissed you.

Your hands made their way under his fitted t-shirt, his hard muscles relaxing under your touch. You rolled him over, straddling his hips as you removed the shirt from his body, throwing it to the side. His hands snaked around your back, unclasping your bra. He placed kisses along your shoulders, his fingers slowly trailing each strap down your arms. He threw your bra to the side and looked over your exposed breasts.

“You’re beautiful, Y/N,” he whispered, “so damn beautiful.”

He places wet kisses along your collarbones, slowly making his way down to your breasts. His fingers held your waist, travelling upwards. You could feel him pressed against your core, heat pooled in your abdomen at the thought. His lips wrapped around your nipple, his tongue running over the hardened bud while his other hand kneed at your left breast. He took his time, paying equal attention to each breast. You relished in the feeling, you loved when he touched you softly, barely grazing your skin with his calloused hands. You could never tire from it.

You pressed your chest against his, your fingers making their way into his hair. He wrapped his arms around you, holding you tight to him as you leaned him back, crashing back into the mattress. Your lips moved in sync with his, your tongues danced together.

You pressed kisses along his jaw moving down towards his neck. You began to gently suck the skin below his ear, making sure to leave your mark on him, not that this would be the only one. You could hear his breathing perfectly, quiet moans as you gingerly bit into his skin. You moved down his chest, kissing every inch of his chest. You stopped at the waistband of his pajama pants, looking up at him for approval. He smiled at you softly, his eyes filled with love and adoration before he sat up and pressed his lips to yours. You playfully pushed him down on the bed, your fingers curled in his pajama pants. You slide them down his long legs before throwing them across the room. Next you slide your hands into his boxers, quickly removing them from his body. His erection sprang free, hitting his stomach.

“You know, every inch of you is gorgeous. I feel like I don’t tell you that enough,” you told him as you glanced over his body.

“You don’t need to tell me all the time,” he smiled, “but thank you.”

He sat up and helped you out of your panties. He looked over your body as if he were trying to memorize it, like this was some sort of dream.

“You’re stunning, baby,” he said as he looked up to meet your eyes. “you literally take my breath away.”

“Stop lying,” you joked as you leaned down to kiss him.

“I would never,” he said, his hand over his heart, a fake hurt look on his face. You climbed onto him, straddling his hips once more, you could feel his cock pressing beneath you. He kissed you hard, holding you tightly once more. “Do we need a condom? I know we’ve been using one recently.”

“I’m still on the pill, we can use a condom if you’d like,” you assured him. He shook his head, and you were okay with that.

You lined yourself up with his cock, slowly sinking down onto his length, letting him fill you up completely. You watched the look on his face, the amount of effort he put in not to let out a moan. He watched your face as he bottomed out, making sure he wasn’t hurting you.

“You okay?” he asked as you pressed your forehead to his.

“I’m good,” you smiled as you kissed him passionately.

You began to move slowly on his length, his arms wrapped around your back, his fingers pressing into your skin. He thrusted into you, meeting your hips as you moved up and down his cock. His lips attacked your neck, sucking away at the sensitive skin. You began to breath a little heavier.

He squeezed you a little tighter as he rolled over, placing you on your back against the bed. He kissed you hard as his thrusts became a little faster, his pubic bone rubbing against your clit as his body moved with yours. You held him close to you, his breathing was becoming heavy, an indication that he was growing closer.

“I love you so much,” you whispered into his ear.

“I love you,” he groaned against your lips.

He began to move faster, you could feel his thrusts throughout your body, his cock brushing your sweet spot over and over again. You could feel your orgasm building, slowly growing closer each time his body met yours. You wrapped your legs around his waist, creating a new angle for him to hit your sweet spot right on.

“Come for me, baby,” he muttered.

You met him, thrust for thrust, your walls clenching around him. You buried your face in the crook of his neck, your fingers digging into the muscles in his back. You moaned his name as he helped you ride out your orgasm, throwing him over the edge. He groaned into your neck as he spilled himself inside you, his thrusts were uneven, his body shaking as he rode out his orgasm, almost making you come again.

He kissed you sweetly as you both came down from your highs. His fingers traced over your sweat covered skin. He rolled off of your body to the empty side of the bed. His eyes were still on you. You smiled softly, pecking his lips before grabbing his shirt off the floor and throwing it on your body.

“I’m sorry for hurting you, Dean,” you whispered as you rested your head on his chest.

“I’m sorry for everything,” he said quietly. “But I’m glad we’re here together now.”

“Me too, I’ll be here forever if I can,” you smiled.

He chuckled as he ran his fingers through your hair, “I just realized we’ve had sex twice today.” You laughed into his chest.

“We could make it a third and do it in the shower,” you suggested. Before you could even protest, he was up on his feet, grabbing you and dragging out out of bed towards his bathroom, shutting the door behind him.

“Great idea.”


End file.
